Pressure sensitive adhesive compositions

ABSTRACT

Disclosed are removable pressure sensitive adhesive compositions (PSAs) useful with facestocks and/or packaging labels designed to be removed in the recycling of polymeric packaging. The PSAs of the invention include (a) at least one monomer which may undergo free radical polymerization and whose homopolymer has a glass transition temperature of less than or equal to 10° C., (b) at least one mono-olefinically unsaturated monomer having aldehyde or ketone functionality, and (c) an effective amount of at least one polyhydrazide crosslinker having hydrazine functionality. The PSA composition of the invention exhibits a peel adhesion value of between about 0.4 lbs/in (70 N/m) and about 4 lbs/in (700 N/m), and the percent film remaining on the polymeric packaging after a sink-float testing is 0% to about 8%.

INCORPORATION BY REFERENCE TO ANY PRIORITY APPLICATIONS

Any and all applications for which a foreign or domestic priority claimis identified in the Application Data Sheet as filed with the presentapplication are hereby incorporated by reference under 37 CFR 1.57.

BACKGROUND OF THE INVENTION Field of the Invention

The present invention relates to aqueous emulsion pressure sensitiveadhesive (PSA) compositions useful with facestocks and/or packaginglabels designed to be removed in the recycling of polymeric packaging.

Description of the Related Art

In recent years, use of polymeric packaging (e.g. polyethyleneterephthalate (PET), high density polyethylene (HDPE), polyvinylchloride (PVC), polypropylene (PP), or other plastic types) hasincreased due to their lightweight and break resistance. Pressuresensitive filmic labels have also grown in usage with polymericpackaging systems due to improved moisture resistance and appearance,and the ability to recycle such packaging materials is desirable. Duringa typical recycling process, a hot caustic bath containing surfactant isused to release the ground plastic flake from the label. Subsequentlythe plastic flake is separated in a sink-float process from the removedlabel. The Association of Postconsumer Plastic Recyclers (APR) haveestablished protocol for evaluating labeling systems for recyclability.Failure to remove the filmic labels in the recycling process taints thecolor and reduces the clarity of recycled PET.

Filmic labels are more resistant to the recycling conditions which leadsto a portion of the label still attached at the end of the process.Therefore, it would be desirable that the filmic label and adhesive bedesigned to release in the washing step of the recycling process, and toseparate from the PET in a liquid, showing a specific gravity allowingfor floating or sinking of the separated components.

Accordingly, there is a need for a pressure sensitive adhesive (PSA) forfilmic labels that can facilitate separation in the recycling processwhile maintaining the desired performance properties through thearticle's life cycle.

There is also a need in the art for polymeric packaging systems that canprovide for a recycling process which is efficient and cost effective.

SUMMARY OF THE INVENTION

In one embodiment, there is provided a filmic facestock material forpolymeric packaging which includes a pressure sensitive adhesive (PSA)composition. The PSA includes (a) at least one monomer which may undergofree radical polymerization and whose homopolymer has a glass transitiontemperature (Tg) of less than or equal to 10° C., (b) at least onemono-olefinically unsaturated monomer having aldehyde or ketonefunctionality, and (c) an effective amount of at least one polyhydrazidecrosslinker having hydrazine functionality. The PSA composition of theinvention exhibits a peel adhesion value of between about 0.4 lbs/in (70N/m) and about 4 lbs/in (700 N/m), and the percent film remaining on thepolymeric packaging after a sink-float testing is 0% to about 8%. Inanother embodiment, the PSA composition of the invention furtherincludes a surfactant with a reactive carbon-carbon double bond.

In another embodiment, there is provided a filmic facestock material forpolymeric packaging which includes a PSA composition. The PSAcomposition includes (a) 50 wt % to about 95 wt % of at least onemonomer which may undergo free radical polymerization and whosehomopolymer has a glass transition temperature (Tg) of less than orequal to 10° C., (b) >0.1 wt % at least one mono-olefinicallyunsaturated monomer having aldehyde or ketone functionality, (c) aneffective amount of at least one polyhydrazide crosslinker havinghydrazine functionality, and a surfactant with a reactive carbon-carbondouble bond, with the wt % being based on the weight of the monomermixture, with the effective amount of the polyhydrazide crosslinker issuch that the ratio of the hydrazine functionality is between about 0.02to 5 equivalents per 1 equivalent of the aldehyde or ketonefunctionality. The PSA composition of the invention exhibits a peeladhesion value of between about 0.4 lbs/in (70 N/m) and about 4 lbs/in(700 N/m), and the percent film remaining on the polymeric packagingafter a sink-float testing is 0% to about 8%.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a scatter plot of Peel Adhesion v. Recyclability for PSAcompositions of the invention and control PSA compositions.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT

The removable PSA compositions of the invention includes an acrylicpolymer dispersion containing a monomer mixture having (a) at least onemonomer which may undergo free radical polymerization. In oneembodiment, the monomer mixture may include at least one acrylic acidester or (meth)acrylate acid ester whose homopolymer has a glasstransition temperature (Tg) of less than or equal to 10° C., and (b) atleast one mono-olefinically unsaturated monomer having an aldehyde orketone group. The emulsion of the invention being reacted with (c) aneffective amount of at least one polyhydrazide crosslinker.

Examples of the at least one acrylic acid ester or (meth)acrylate acidester whose homopolymer has a glass transition temperature (Tg) of lessthan or equal to 10° C. include but are not limited to benzyl acrylate,n-butyl acrylate, sec-butyl acrylate, cyanoethyl acrylate, iso-decylacrylate, n-decyl acrylate, dodecyl acrylate, dodecyl methacrylate,2-ethoxyethyl acrylate, ethyl acrylate, 2-ethylhexyl acrylate,2-ethylhexyl methacrylate, n-hexyl acrylate, hexyl methacrylate,isobutyl acrylate, isopropyl acrylate, isotactic, 2-methoxyethylacrylate, methyl acrylate, octadecyl methacrylate, octyl methacrylate,2-phenylethyl acrylate, n-propyl acrylate, and 2,2,2-trifluoroethylacrylate, as well as mixtures or any subset thereof.

In one embodiment, Tg of the acrylic acid ester or (meth)acrylate acidester homopolymer is between about −100° C. and 10° C., or between about−70° C. to 10° C., or between about −70° C. to −10° C.

In one embodiment, the at least one acrylic acid ester or (meth)acrylateacid ester whose homopolymer has a glass transition temperature (Tg) ofequal to or less than 10° C. is present in an amount of about 50 wt % toabout 95 wt % or about 70 wt % to about 90 wt % based on the weight ofthe monomer mixture.

In one embodiment, the at least one acrylic acid ester or (meth)acrylateacid ester whose homopolymer has a glass transition temperature (Tg) ofequal to or less than 10° C. includes 2-ethylhexyl acrylate, n-butylacrylate, or any mixtures thereof.

Mono-olefinically unsaturated monomers having ketone or aldehydefunctionality are monomers containing an aldo or keto moiety and apolymerizable carbon-carbon double bond. Examples include, but are notlimited to, acrolein, methacrolein, vinylbenzaldehyde, crotonaldehyde,(meth)acryloxyalkylpropanals, diacetone acrylamide (DAAM), diacetoneacrylate, or any mixtures or subsets thereof.

In one embodiment the amount of mono-olefinically unsaturated monomershaving aldehyde or ketone functionality is present in an amount of >0.1wt %, or about 0.5 to 10 wt. %, or about 0.75% to 5 wt. %, based on theweight of the monomer mixture.

In one embodiment, the mono-olefinically unsaturated monomers havingketone or aldehyde functionality includes diacetone acrylamide,diacetone acrylate, acrolein, or any mixtures thereof.

In one embodiment the monomer mixture may optionally include one or moreacrylic acid ester or (meth)acrylate acid ester whose homopolymer has aTg of greater than 10° C. such as, for example greater than 10° C. toabout 175° C. Examples include but are not limited to benzylmethacrylate, t-butyl acrylate, 2-tert-Butylaminoethyl methacrylate,butyl methacrylate, t-butyl methacrylate, cyclohexyl acrylate cyclohexylmethacrylate, diethylaminoethyl methacrylate, dimethylaminoethylmethacrylate, ethyl methacrylate, hexadecyl acrylate, hexadecylmethacrylate, hexyl acrylate, 2-hydropropyl methacrylate, 2-hydroxyethylmethacrylate, isobornyl acrylate, isobornyl methacrylate, isobutylmethacrylate, isopropyl methacrylate, methyl methacrylate, atactic,methyl methacrylate, syndiotactic, phenyl methacrylate andtrimethylsilyl methacrylate, as well as mixtures or any subset thereof.

In one embodiment, the at least one acrylic acid ester or (meth)acrylateacid ester whose homopolymer has a glass transition temperature (Tg) ofgreater than 10° C. is present in an amount of about 0 wt % to about 50wt %, or about 0 wt % to about 30 wt % based on the weight of themonomer mixture.

In one embodiment, the monomer mixture may include one or moreethylenically unsaturated carboxylic acid. Examples included but are notlimited to monoethylenically unsaturated monocarboxylic acids such asacrylic acid, methacrylic acid, ethacrylic acid, crotonic acid, andcarboxyethyl acrylate, monoethylenically unsaturated dicarboxylic acidssuch as maleic acid, fumaric acid, itaconic acid, and citraconic acid,monoethylenically unsaturated tricarboxylic acids such as aconitic acid,and the halogen substituted derivatives (e.g., alphachloracylic acid)and anhydrides of these acids (e.g., maleic anhydride and citraconicanhydride).

The PSA composition of the invention may comprise about 0.5 to about 7wt % or about 1 to about 3 wt % ethylenically unsaturated carboxylicacids, based on the weight of the monomer mixture.

In one embodiment, the PSA composition of the invention may include analkyl mercaptan chain transfer agent such as a C₆-C₁₈ alkyl mercaptanfor example n-hexyl mercaptan, n-octyl mercaptan and n-dodecylmercaptan. When utilized, the PSA composition of the invention maycomprise about 0.01 to about 0.5 wt % mercaptan chain transfer agents,based on the weight of the monomer mixture.

In another embodiment of the invention, the process to prepare thedispersions of the invention may utilize a continuous phase (usuallywater), and other components standard and known in the art such asinitiators, reducing agents, surfactants, catalysts, wetting agents,crosslinking agents, preservatives and the like. For example, anyconventional water soluble polymerization initiator suitable foremulsion polymerization may be used. The typical wt % of said initiatorsare from 0.01% to 2.0 wt. % and preferably 0.01 to about 1.0 wt % basedon the total weight of monomers. Examples of initiators include, but arenot limited to, persulfates, peroxides, azo compounds, and the mixturesthereof. The water soluable initiators can be used alone or incombination with one or more conventional reducing agents such as, butnot limited to, sodium formaldehyde sulfoxylate, sodium metabisulfite,ascorbic acid, ferrous salts, chelated iron salts, and the like.

In one embodiment, the water soluable polymerization intiator systemsare peroxides utilized in combination with conventional reducing agentssuch as tert-butyl hydroperoxide sodium formaldehyde sulfoxylate basedsystems with a chelated ferric complex catalyst.

Examples of suitable surfactant systems are those known in the art andinclude anionic, nonionic, cationic, or amphoteric emulsifiers andmixtures thereof. Examples of anionic surfactants include, but are notlimited to, alkyl sulfates, sulfates of ethoxylate alcohols, arylsulfonates, phosphates of ethoxylated alcohols, sulfosuccinates,sulfates and sulfonates of ethoxylated alkylphenols, and mixturesthereof. Examples of nonionic surfactants include, but are not limitedto, ethoxylated alcohols, ethoxylated alkylphenols, and mixturesthereof. Examples of cationic surfactants include, but are not limitedto, ethoxylated fatty amines In one embodiment, reactive surfactantchemistry which have reactive carbon-carbon double bond is utilized.Examples of reactive chemistries include, but are not limited to,alkylphenol ethoxylates containing alkenyl substituents,polyoxyalkylene-1-(allyloxymethyl) alkyl ether sulfate salt compounds,salts of poly(oxy-1,2-ethanediyl),alpha-sulfo-omega-[1-(hydroxymethyl)-2-(2-propen-yloxy)ethoxy] (Adeka SRSeries, commercially available from Adeka Corporation), and mixtures orsubsets thereof. In one embodiment, the reactive surfactant includes anAdeka SR Series reactive surfactant. The typical weight of surfactant is0.2 to 5.0 wt. % and more preferably 1.0 to 5.0 wt. % and mostpreferably 1.0 to 3.0 wt. %. The surfactants are utilized byconventional methods that are well known in art. In one embodiment, theprocess to prepare the PSA includes the emulsification of the monomermix with the surfactant system prior to the polymerization reaction.

Following polymerization, the pH of the latex emulsion is adjusted witha suitable base including, but are not limited to, metal hydroxides,ammonium hydroxide, amines, and mixtures thereof. The pH is adjusted toat least 6.0, and more preferably 6.5 to 9.5, and most preferably 7.0 to9.0. In one embodiment, the suitable base is ammonium hydroxide.

The PSA emulsion of the invention has a typical solids content fromabout 30 to 70% and preferably 40 to 55%. Polymerization can beconducted at typical temperatures for emulsion polymerization. Thepolymerization is preferably conducted in the range of 110° F. (43.3°C.) to 210° F. (99° C.) and more preferably 130° F. (54° C.) to 190° F.(88° C.).

The PSA compositions of the invention are reacted with an effectiveamount of polyhydrazide compound having a t least two hydrazide (NH-NH₂)functional groups. Specific examples of polyhydrazide compounds include,but are not limited to, oxalic acid dihydrazide, malonic aciddihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide;adipic acid dihydrazide, sebacic acid dihydrazide; monoolefinunsaturated dicarboxylic acid dihydrazide such as maleic aciddihydrazide, fumaric acid dihydrazide, itaconic acid dihydrazide;carbonic acid 10 polyhydrazide such as carbonic acid dihydrazide;aromatic dihydrazides such as phthalic acid dihydrazide, terephthalicacid dihydrazide, isophthalic acid dihydrazide; trihydrazides such as1,2,4-butanetricarbohydrazide,1,1,4-butanetricarbohydrazide,1,2,5-pentanetricarbohydrazide,1,3,6-hexanetricarbohydrazide, 1,3,7 -heptanetricarbohydrazide, andI-hydroxy-1,2,4-butanetricarbohydrazide, and mixtures or any subsetsthereof. In one embodiment, the polyhydrazide includes adipicdihydrazide, isophthalic dihydrazide, sebacic dihydrazide,bis-semicarbizides, and mixtures thereof. In another embodiment, thepolyhydrazide is adipic acid dihydrazide.

The effective amount of the polyhydrazide crosslinker is such that theratio of hydrazine functionality is between about 0.02 to 5, or about0.1 to 3 or about 0.5 to 2 equivalents per 1 equivalent of the ketone oraldehyde functionality of the mono-olefinically unsaturated monomershaving ketone or aldehyde functionality. The polyhydrazide compound canbe added at any point in the process. In one embodiment, it is addedafter the emulsion reaction. In one embodiment, the polyhydrazidecrosslinker is optional.

The PSA compositions of the invention may be used with filmic or paperfacestock materials. Examples of suitable filmic facestock materialsinclude, but are not limited to, olefinic facestocks (e.g.polypropylene, polyethylene, etc), polystyrene facestocks, PETfacestocks, polyvinyl chloride and mixtures thereof. The facestockconstructions can contain multiple layers. The facestock can alsocontain a topcoat, printing, and/or overlaminates.

In one embodiment the PSA compositions of the invention typicallyexhibit peel adhesion values of less than about 4 lbs/in (700 N/m), lessthan about 2 lbs/in (350 N/m), less than about 1 lb/in (175 N/m) orbetween about 0.4 lbs/in (70 N/m) to about 4 lbs/in (700 N/m)or betweenabout 0.4 lbs/in (70 N/m) to about 2 lbs/in (350 N/m). In anotherembodiment, during the recycling of polymeric packaging with filmiclabels adhered with the PSA compositions of the invention, the percentfilm (% film) remaining on PET after sink-float testing is about 0% toabout 8%, or about 0% to about 5%, or about 0% to about 3%.

In one embodiment, the PSA compositions of the invention are free ofadditives as described in US Patent Publication No. 2010/0051200 asfacilitating the caustic washing of the polymeric substrate during therecycling process. In is known in the art that use of such additives mayimpart moisture sensitivity to a PSA composition.

In order to provide a better understanding of the present inventionincluding representative advantages thereof, the following examples areoffered.

EXAMPLES Example 1

In a 2 L jacketed glass reactor equipped with a reflux condenser,thermocouple, and 4-blade agitator, 1800.0 g of latex was prepared. Thereactor was charged with 410.7 g of water, 5.6 g of Abex 2535 surfactant(available from Rhodia Solvay Group), and 0.0040 g of Dissolvine 4.5catalyst (available from Akzo Nobel N.V.), heated to 140° F. (60° C.),and agitated from 100 to 300 rpms. The monomer preemulsion was preparedin a separate vessel by mixing 257.7 g of water, 16.1 g of Adeka SR 3025(available from Adeka Corporation) surfactant, 2.4 g of Abex 2535surfactant, 8.05 g of Surfynol 440 (available from Air Products andChemicals, Inc.) wetting agent, 12.1 g of betacarboxyethyl acrylate, 8.1g acrylic acid, 40.3 g butyl acrylate, 40.3 g ethyl acrylate, and 724.8g 2-ethylhexyl acrylate. After the preemulsion was mixed and formed,32.8 g of preemulsion was added to the reactor. And additional 32.2 g ofAdeka SR3025 was added to the preemulsion. 24.2 g of water with 0.4 g oftertbutyl hydroperoxide and 24.2 g of water with 0.2 g of sodiumformaldehyde sulfoxylate was added to the reactor to create an in-situemulsion seed. After the in-situ seed was formed indicated by an initialexotherm, the preemulsion was fed over 180 minutes and an oxidizer feedof 48.3 g of water with 2.4 g of tertbutyl hydroperoxide and a reducerfeed of 96.6 g of water with 1.2 g of sodium formaldehyde sulfoxylatewere added over 300 minutes. The reaction was carried out at 138° F.(59° C.) to 142° F. (142° C.). After 90 minutes of the preemulsion beingfed, 24.2 g of a 30% diluted in water diacetone acrylamide solution wasadded to the preemulsion. When the oxidizer and reducer feeds completed,the reactor was cooled to <110° F. (43° C.) and 8.1 g of water with 6.4g of 28% aqueous solution ammonium hydroxide was added. 4.0 g of waterwith 1.6 g of Acticide LA preservative (available from Thor Specialties,Inc.) was added to the reactor. Examples 2 to 10 were synthesized in thesame manner as Example 1 with the changes to the compositions set forthin Tables 1 and 2.

TABLE 1 Example 1 (Invention) 2 (Control) 3 (Control) 4 (Control) 5(Invention) 2-Ethylhexyl Acrylate 724.8 734.6 733.9 728.0 644.2 MethylMethacrylate 0.0 0.0 0.0 0.0 80.5 DAAM 30% Solution 24.2 0.0 0.0 0.024.2 n-Dodecyl Mercaptan 0.0 0.0 0.0 0.0 0.0 Allyl Methacrylate 0.0 0.01.6 0.0 0.0 Hexanediol Diacrylate 0.0 0.0 0.0 16.2 0.0

TABLE 2 Example 6 (Invention) 7 (Invention) 8 (Control) 9 (Invention) 10(Control) 2-Ethylhexyl Acrylate 604.0 721.5 731.3 563.7 733.8 MethylMethacrylate 120.8 0.0 0.0 161.1 0.0 DAAM 30% Solution 24.2 24.2 0.024.2 0.0 n-Dodecyl Mercaptan 0.0 0.0 0.0 0.0 0.8 Allyl Methacrylate 0.03.2 3.3 0.0 0.0 Hexanediol Diacrylate 0.0 0.0 0.0 0.0 0.0

The pH of each example was adjusted with 26 Be ammonium hydroxide to apH of 8.3 to 8.5., and 1.0% of Surfynol 440 wetting agent was added. Inthe examples of the invention (i.e. examples 1 5, 6, 7 and 9) astoichomteric equivalent amount of adipic dihydrazide to diacetoneacrylamide was added. Samples were coated onto paper coated withsilicone release liner at 10 g/m² and dried for 1-minute at 90° C.Afterward, the samples were laminated to 1.6 mils cavitated whitebiaxial oriented polypropylene and acclimated at room temperature forgreater than 24-hours. The samples were applied to the substrates andaged 1-hour at 50° C. followed by 1-hour cool to room temperature beforetesting.

The examples were tested according to the small scale laboratory test asdescribed in “APR Screening Plastic Label and Closure Floatability Testfor PET Bottles” (see www.plasticsrecycling.org). However, the groundpiece size was reduced from ⅜ inch to ¼ inch, which is believed to moreaccurately represent flake found at the recycling plants. In addition,the test temperature was reduced to 85° C. from 88° C. Peel adhesion wastested according to the Pressure Sensitive Tape Council standard PSTC101 on PET substrate (ASTM Designation D3330 Standard Test Method forPeel Adhesion of Pressure-Sensitive Tape). The results are set forth inTable 3. The data in Table 3 is set forth in a scatter plot in FIG. 1.

TABLE 3 Peel % Film Remaining Adhesion on PET After Sink- Example lbs/in(N/m) Float Example 1 Invention 0.532 (93)  1.0% Example 2 Control 0.609(106) 24.5% Example 3 Control 0.484 (85)  8.5% Example 4 Control0.777(136) 37.0% Example 5 Invention 0.697 (122)  1.0% Example 6Invention 0.774 (135)  0.0% Example 7 Invention 0.38 (66)  0.0% Example8 Control 0.365 (64)  1.0% Example 9 Invention 0.818 (143)  3.0% Example10 Control 1.29 (226) 64.0%

An APR approved lab, Plastics Forming Enterprise (PFE) (seewww.plasticsforming.com), following APR protocol, conducted anindependent evaluation in the recycling process using the PSAcomposition of Example 1 and resulting PET recycled plaques, compared tocontrol non-labeled PET plaques. The results for the L*a*b* color scaleand haze are set forth in Table 4 [L* (100=white; 0=black) a*(positive=red; negative=green; 0=gray) b* (positive=yellow;negative=blue; 0=gray)]

TABLE 4 L* a* b* L* a* b* Haze Ex- Val- Val- Val- av- Av- Av- Av- ampleues ues ues erage erage erage Haze erage Ex- 87.71 −1.16 3.68 87.75−1.15 3.58 2.67 2.56 ample 87.76 −1.17 3.82 2.65 1 87.74 −1.16 3.61 2.5987.79 −1.12 3.34 2.42 87.77 −1.13 3.43 2.48 Control 87.76 −1.23 3.7487.78 −1.21 3.66 2.47 2.45 PET 87.85 −1.21 3.68 2.17 87.78 −1.21 3.632.57 87.83 −1.19 3.5  2.08 87.67 −1.22 3.76 2.96

Based on the above results, referring to the Examples of the invention,the addition of diacetone acrylamide chemistry to the PSA allows forrecyclability at higher peel values which is desirable for labelingsystems designed for polymeric packaging. In contrast, referring tocontrol example 7, a peel level of below 0.40 lbs/in is needed to allowfor sufficient label release from the PET flake during recycling.

What is claimed is:
 1. A filmic facestock material for polymericpackaging comprising: a pressure sensitive adhesive compositioncomprising a monomer mixture, wherein the monomer mixture comprises (a)at least one monomer which may undergo free radical polymerization andwhose homopolymer has a glass transition temperature of less than orequal to 10° C., (b) at least one mono-olefinically unsaturated monomerhaving aldehyde or ketone functionality, and (c) an effective amount ofat least one polyhydrazide crosslinker having hydrazine functionality;wherein the pressure sensitive adhesive composition exhibits a peeladhesion value of between about 0.4 lbs/in (70 N/m) and about 4 lbs/in(700 N/m); and wherein a percent film remaining on the polymericpackaging after a sink-float testing is 0% to about 8%.
 2. The filmicfacestock material of claim 1 wherein the at least one monomer which mayundergo free radical polymerization and whose homopolymer has a glasstransition temperature of less than or equal to 10° C. comprises atleast one acrylic acid ester or (meth)acrylate acid ester.
 3. The filmicfacestock material of claim 2 wherein the least one acrylic acid esteror (meth)acrylate acid ester is selected from the group consisting ofbenzyl acrylate, n-butyl acrylate, sec-butyl acrylate, cyanoethylacrylate, iso-decyl acrylate, n-decyl acrylate, dodecyl acrylate,dodecyl methacrylate, 2-ethoxyethyl acrylate, ethyl acrylate,2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, n-hexyl acrylate,hexyl methacrylate, isobutyl acrylate, isopropyl acrylate, isotactic,2-methoxyethyl acrylate, methyl acrylate, octadecyl methacrylate, octylmethacrylate, 2-phenylethyl acrylate, n-propyl acrylate, and2,2,2-trifluoroethyl acrylate, and combinations thereof.
 4. The filmicfacestock material of claim 3 wherein the least one acrylic acid esteror (meth)acrylate acid ester is selected from the group consisting of2-ethylhexyl acrylate, n-butyl acrylate, and combinations thereof. 5.The filmic facestock material of claim 1 wherein the at least one atleast one mono-olefinically unsaturated monomer having an aldehyde orketone functionality is selected from the group consisting of acrolein,methacrolein, vinylbenzaldehyde, crotonaldehyde,(meth)acryloxyalkylpropanals, diacetone acrylamide, diacetone acrylate,and combinations thereof.
 6. The filmic facestock material of claim 5wherein the at least one at least one mono-olefinically unsaturatedmonomer having an aldehyde or ketone functionality is selected from thegroup consisting of diacetone acrylamide, diacetone acrylate, acrolein,and combinations thereof.
 7. The filmic facestock material of claim 1wherein the monomer mixture comprises: 50 wt % to about 95 wt % of theat least one monomer which may undergo free radical polymerization andwhose homopolymer has a glass transition temperature of less than orequal to 10° C., and >0.1 wt % of the at least one mono-olefinicallyunsaturated monomer having an aldehyde or ketone group, wherein the wt %is based on the weight of the monomer mixture.
 8. The filmic facestockmaterial of claim 1 wherein the monomer mixture further comprises one ormore ethylenically unsaturated carboxylic acid.
 9. The filmic facestockmaterial of claim 1 wherein the monomer mixture further comprises or atleast one monomer which may undergo free radical polymerization andwhose homopolymer has a glass transition temperature of greater than 10°C.
 10. The filmic facestock material of claim 1 wherein the effectiveamount of the polyhydrazide crosslinker is such that the ratio of thehydrazine functionality is between about 0.02 to 5 equivalents per 1equivalent of the aldehyde or ketone functionality.
 11. The filmicfacestock material of claim 1 wherein the polyhydrazide is selected fromthe group consisting of oxalic acid dihydrazide, malonic aciddihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide;adipic acid dihydrazide, sebacic acid dihydrazide; monoolefinunsaturated dicarboxylic acid dihydrazide such as maleic aciddihydrazide, fumaric acid dihydrazide, itaconic acid dihydrazide;carbonic acid 10 polyhydrazide such as carbonic acid dihydrazide;aromatic dihydrazides such as phthalic acid dihydrazide, terephthalicacid dihydrazide, isophthalic acid dihydrazide; trihydrazides such as1,2,4-butanetricarbohydrazide,1,1,4-butanetricarbohydrazide,1,2,5-pentanetricarbohydrazide,1,3,6-hexanetricarbohydrazide, 1,3,7-heptanetricarbohydrazide, andI-hydroxy-1,2,4-butanetricarbohydrazide, and combinations thereof. 12.The filmic facestock material of claim 11 wherein polyhydrazide isselected from the group consisting of adipic dihydrazide, isophthalicdihydrazide, sebacic dihydrazide, bis-semicarbizides, and combinationsthereof.
 13. The filmic facestock material of claim 1 wherein thepolymeric packaging comprises polyethylene teraphthalate, high densitypolyethylene, polyvinyl chloride, polypropylene or combinations thereof.14. The filmic facestock material of claim 1 wherein the filmicfacestock comprises an olefinic facestock, a polystyrene facestock, apolyethylene teraphthalate facestocks, a polyvinyl chloride orcombinations thereof.
 15. The filmic facestock material of claim 1wherein the pressure sensitive adhesive composition further comprises asurfactant with a reactive carbon-carbon double bond.
 16. The filmicfacestock material of claim 15 wherein the surfactant with a reactivecarbon-carbon double bond is selected from the group consisting ofalkylphenol ethoxylates containing alkenyl substituents,polyoxyalkylene-1-(allyloxymethyl) alkyl ether sulfate salt compounds,salts of poly(oxy-1,2-ethanediyl),alpha-sulfo-omega-[1-(hydroxymethyl)-2-(2-propen-yloxy)ethoxy] andcombinations thereof.
 17. The filmic facestock material of claim 1wherein the facestock material is an olefinic facestock.
 18. A filmicfacestock material for polymeric packaging comprising: a pressuresensitive adhesive composition comprising a monomer mixture, wherein themonomer mixture comprises (a) at least one monomer which may undergofree radical polymerization and whose homopolymer has a glass transitiontemperature of less than or equal to 10° C., (b) at least onemono-olefinically unsaturated monomer having aldehyde or ketonefunctionality, (c) an effective amount of at least one polyhydrazidecrosslinker having hydrazine functionality, and a surfactant with areactive carbon-carbon double bond; wherein the pressure sensitiveadhesive composition exhibits a peel adhesion value of between about 0.4lbs/in (70 N/m) and about 4 lbs/in (700 N/m); and wherein a percent filmremaining on the polymeric packaging after a sink-float testing is 0% toabout 8%.
 19. A filmic facestock material for polymeric packagingcomprising: a pressure sensitive adhesive composition comprising amonomer mixture, wherein the monomer mixture comprises (a) 50 wt % toabout 95 wt % of at least one monomer which may undergo free radicalpolymerization and whose homopolymer has a glass transition temperatureof less than or equal to 10° C., (b) >0.1 wt % at least onemono-olefinically unsaturated monomer having aldehyde or ketonefunctionality, (c) an effective amount of at least one polyhydrazidecrosslinker having hydrazine functionality, and a surfactant with areactive carbon-carbon double bond, where the wt % is based on theweight of the monomer mixture; wherein the effective amount of thepolyhydrazide crosslinker is such that the ratio of the hydrazinefunctionality is between about 0.02 to 5 equivalents per 1 equivalent ofthe aldehyde or ketone functionality; wherein the pressure sensitiveadhesive composition exhibits a peel adhesion value of between about 0.4lbs/in (70 N/m) and about 4 lbs/in (700 N/m); and wherein a percent filmremaining on the polymeric packaging after a sink-float testing is 0% toabout 8%.
 20. The filmic facestock material of claim 19 wherein thesurfactant with a reactive carbon-carbon double bond is selected fromthe group consisting of alkylphenol ethoxylates containing alkenylsubstituents, polyoxyalkylene-1-(allyloxymethyl) alkyl ether sulfatesalt compounds, salts of poly(oxy-1,2-ethanediyl),alpha-sulfo-omega-[1-(hydroxymethyl)-2-(2-propen-yloxy)ethoxy] andcombinations thereof.